183787-79-3

Upstream product

• 177555-90-7 Trifluoro-methanesulfonic acid (1R,3R)-2-benzyl-8-methoxy-1,3-dimethyl-1,2,3,4-tetrahydro-isoquinolin-6-yl ester 
• 183787-78-2 (1R,3R)-N-benzyl-6-(5'-isopropoxy-4'-methoxy-2'-methyl-8'-naphthyl)-8-methoxy-1,3-dimethyl-1,2,3,4-tetrahydroisoquinoline 
• 104292-12-8 (1R,3R)-2-Benzyl-8-methoxy-1,3-dimethyl-1,2,3,4-tetrahydro-isoquinolin-6-ol 
• 183787-80-6 (1R,3R)-N-benzyl-6-(5'-hydroxy-4'-methoxy-2'-methyl-8'-naphthyl)-8-methoxy-1,3-dimethyl-1,2,3,4-tetrahydroisoquinoline 

Relevant academic research and scientific papers

Synthesis of pindikamine A, a michellamine-related dimer of a non-natural, 'skew' naphthylisoquinoline

The synthesis of an unnatural dimeric naphthylisoquinoline, pindikamine A (3), as a 'skew' analog of antiviral michellamines, is described. Because of the unusual coupling positions, this C2-symmetric quateraryl is the first michellamine analog without axial chirality. Key steps of total synthesis are the preparation of the molecular precursor 9 by intermolecular biaryl coupling, followed by a highly efficient oxidative 'dimerization' to give 8, which is transformed to 3. Pindikamine A (3) and its monomeric 'half' 10 show good antimalarial activity against plasmodium falciparum in vitro.